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Copper-catalyzed enantioselective arylalkynylation of alkenes.

ABSTRACT: A copper-catalyzed enantioselective arylalkynylation of alkenes with diaryliodonium salt and a monosubstituted alkyne is reported. The three-component coupling reactions proceed under mild reaction conditions with a broad substrate scope, leading to synthetically valuable 1,2-diaryl-3-butynes. The key to the success of this chemistry is the employment of the chiral bisoxazoline-phenylaniline (BOPA) ligand. A novel reaction pathway involving the phenyl radical generation under thermal copper catalysis is proposed according to mechanistic studies.

SUBMITTER: Lei G

PROVIDER: S-EPMC7069229 | biostudies-literature | 2020 Feb

REPOSITORIES: biostudies-literature

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Copper-catalyzed enantioselective arylalkynylation of alkenes.

Lei Guangyue G Zhang Hanwen H Chen Bin B Xu Meichen M Zhang Guozhu G

Chemical science 20200108 6

A copper-catalyzed enantioselective arylalkynylation of alkenes with diaryliodonium salt and a monosubstituted alkyne is reported. The three-component coupling reactions proceed under mild reaction conditions with a broad substrate scope, leading to synthetically valuable 1,2-diaryl-3-butynes. The key to the success of this chemistry is the employment of the chiral bisoxazoline-phenylaniline (BOPA) ligand. A novel reaction pathway involving the phenyl radical generation under thermal copper cata ...[more]

PMID: 32206280

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